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What Lies Ahead: The 2011/2012 Chicago Cubs Offseason Roadmap

With perhaps one of the most pivotal off-seasons in recent memory in store for the Cubs, I thought it might be worth laying out the time line for what will happen over the next few months.

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October 26 – Theo Epstein’s first non-media-dominated day as President of Baseball Operations for the Cubs. Among his first tasks will be discussing the compensation the Cubs owe the Red Sox for his services, as well as the compensation the Cubs will owe the San Diego Padres for Jed Hoyer and Jason McLeod. The compensation decisions are expected to be made within a week. With respect to Epstein compensation, Commissioner Selig says he’ll decide the matter if the two sides can’t agree by November 1.

Approximately October 27/28 – The Cubs are expected to name Jed Hoyer as the team’s General Manager, coming over from San Diego with Assistant General Manager Jason McLeod. (Note: Because of tonight’s delayed World Series game (just happened), this could be pushed back to next Monday, October 31).

October 27 to November 1 – Theo Epstein will meet with current manager Mike Quade and make a decision on his future with the team. Presumably, Quade will be dismissed, and Epstein, with input from Hoyer, will search for a managerial replacement. The Cubs will also have to make decisions on current coaches – only hitting coach Rudy Jaramillo and bench coach Pat Listach are under contract for 2012. The new manager will also have input on the coaches.

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Approximately October 27 to November 1 – As soon as the World Series ends, the five-day period of exclusive negotiating rights with a team’s own free agents occurs. Similarly, this marks the period in which the Cubs will have to make a decision on Aramis Ramirez’s $16 million option for 2012 (which can be bought out for $2 million, and which can be voided by Ramirez). This is also the period in which Ryan Dempster will make a decision on his $14 million player option for 2012. Of the Cubs’ free agents, none are expected to be re-signed in this period.

Approximately November 1 to November 30 – The month of November will probably include a great deal of “getting their feet wet” for the new front office staff. Further, that staff will be searching for additions – more scouts, assistants, etc. – and the managerial search may yet be ongoing. There will also be an organizational review during this period (and beyond), where Epstein and Hoyer, among others, will go over each level of the Cubs’ organization, making decisions about minor league coaches, philosophies, players, promotions, etc. Indeed, a great deal of this decision-making process will carry forward over the next couple of years.

Approximately November 2 to March 2012 – The “Offseason.” The “Hot Stove.” The “Lukewarm Stove.” Whatever you want to call it, this is the period where a team’s roster is built for the subsequent year via free agency, trades, minor league decisions, etc. We’ll find out who is – and, perhaps more importantly this year, who isn’t – a Cubs for 2012.

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November 7 to November 11 – The Chicago Cubs’ Organizational Meetings will take place were going to take place at this time. Theo Epstein has, according to reports this morning, moved the meetings to the second week of February. Whenever they happen, the meetings will be, among other things, a time for the organization to conduct a hyper-focused version of the preceding two entries. Given the new front office, it’s understandable that they are pushing the meeting back.

November 14 to November 22 – The various MLB awards are announced. I don’t think you’ll have to concern yourself with these dates too closely this year.

November 23 – The deadline for offering arbitration to free agents in order to secure compensation if that player leaves the team. In other words, if the Cubs want to get compensation for their Type A/B free agents who walk, this is the date by which they have to offer arbitration (a one-year contract for a to-be-determined amount, which the player may accept or reject). The primary guy on whom the Cubs will have to decide here is Carlos Pena. Depending on how the option decisions shake out, this could also include Ryan Dempster and Aramis Ramirez.

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December 5 – The deadline for having the team’s 40-man roster set for purposes of the Rule Five Draft (about which, more below). Thus, you could see some roster moves being made in the week or two leading up to this date.

December 5 to December 8 – The Winter Meetings. The gist: MLB executives, agents, and players (as necessary) get together in Orlando for a week. The Winter Meetings are a notable source of rumors, signings, trades, etc. While not all of the big offseason moves go down at the Meetings, the groundwork for those moves is frequently laid at the Meetings. In short, it’s an exciting time for folks who love rumors – like a mini version of the trade deadline, but spread out over four days. (No, I will not be having a 96-hour blogathon.)

December 7 – The deadline for free agents to accept offers of arbitration from their 2011 team.

December 8 – The Rule Five Draft. The gist: players who’ve been in an organization’s system for a while (several years) without yet reaching the 40-man roster are eligible to be selected by other teams for a small fee, placed on that team’s 25-man roster, and then kept for good if the player can stick on the 25-man roster for almost all of the subsequent season.

December 12 – Deadline for tendering contracts to arbitration-eligible players (i.e., generally-speaking, players with three or more years of service time, but fewer than six years of service time). This will include guys like Matt Garza, Geovany Soto, Jeff Baker, Randy Wells, Jeff Samardzija, and … Koyie Hill. Note that tendering a contract to these players is optional.

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Approximately December 15 to January 31, 2012 – This is about the time that the Cubs will be sending out non-roster invitations to 2012 Spring Training. The invitations go to prospects and players in the Cubs’ system who’ve not yet been placed on the 40-man roster, as well as veterans who are looking for a 2012 job, but have to “prove it.”

January 13 to January 15, 2012 – The Cubs Convention. Fans will get a chance to see, meet, and hear from Cubs players, coaches and management, and the Cubs frequently like to use the Convention as an opportunity to introduce a big offseason acquisition to the fans. The Convention will also be an opportunity to hang out with me, which I know is what you’re really excited about.

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